Chester Hotel Guide - 4 Stars Hotels in Chester, Vermont

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester 4 Star Hotels

Tonight
7 Mar - 8 Mar
Tomorrow
8 Mar - 9 Mar
Next weekend
13 Mar - 15 Mar
In two weeks
20 Mar - 22 Mar

Our top choices for Chester 4-star hotels

Exterior

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (566 reviews)
"Excellent hotel, staff well trained. "
United States
Christian
The price is Rp5.229.825
Rp6.497.508 total
includes taxes & fees
15 Mar - 16 Mar
Woodstock Inn & Resort
Lobby

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (600 reviews)
"We have been staying at the Equinox for over 35 yrs. Love the whole scene and vibe. Love the pool and hot tub. Love the big real wood fireplace. "
United States
Patricia
The price is Rp2.045.217
Rp3.158.898 total
includes taxes & fees
15 Mar - 16 Mar
The Equinox Golf Resort & Spa
Meeting facility

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG
4.0 star property
Manchester Village Historic District
9.4 out of 10, Exceptional, (834 reviews)
"Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return! "
United States
Heather
The price is Rp2.623.375
Rp3.537.325 total
includes taxes & fees
5 Apr - 6 Apr
Kimpton Taconic Hotel by IHG
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,003 reviews)
"Everything was amazing from the room to the pool to the restaurant and staff. "
United States
Ilana
The price is Rp16.908.075
Rp19.219.522 total
includes taxes & fees
3 Apr - 4 Apr
On The River Inn
American cuisine

The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
4.0 star property
Manchester Village Historic District
9.8 out of 10, Exceptional, (354 reviews)
"Great room, nice staff."
United States
Gary
The price is Rp2.856.945
Rp3.142.640 total
includes taxes & fees
9 Mar - 10 Mar
The Reluctant Panther Inn and Restaurant
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (272 reviews)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (24 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn
Interior

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
10.0 out of 10, Exceptional, (75 reviews)
"Everything was really lovely, clean and nice. Loved the downstairs lounge and bar areas, so warm and relaxing. The host was extremely gracious. Looking forward to going back soon! "
United States
James
The Inn at Weathersfield
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very good, (40 reviews)
"We had a fantastic room! Staff was very friendly and accommodating. Though we visited during peak foliage season, we’ll be trying to book again in the near future to try out the pool."
United States
J
The price is Rp3.195.045
Rp3.482.599 total
includes taxes & fees
17 Mar - 18 Mar
Windham Hill Inn
Terrace/patio

The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (96 reviews)
"Super nice people. Would definitely stay there again. "
United States
Rich
The Village Inn of Woodstock
House, 5 Bedrooms (Meadow) | Terrace/patio

Equinox Resort Residences

Equinox Resort Residences
4.5 star property
Manchester Village Historic District
8.0 out of 10, Very good, (2 reviews)
"The setting is beautiful. The staff were amazing - kind and attentive. Our room was very dated and in need of updating including the bathrooms. The furniture in the room was an odd collection of pieces that could have come from a yard sale. It was not up to the standard we expected given the cost of the room and the overall resort vibe. "
United States
Kurt
Equinox Resort Residences
Exterior

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property
4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (26 reviews)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
United States
Kathia
Winterplace at Okemo, A Vail Resorts Property
Exterior

Seesaw's Lodge

Seesaw's Lodge
4.0 star property
Peru
10.0 out of 10, Exceptional, (26 reviews)
"Great cabin with an even greater staff!!"
United States
Eyasser
The price is Rp4.518.975
Rp4.925.683 total
includes taxes & fees
31 Mar - 1 Apr
Seesaw's Lodge
Front of property – evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104 reviews)
"Great stay"
United States
Wayne
The price is Rp5.197.273
Rp5.639.001 total
includes taxes & fees
9 Mar - 10 Mar
Chesterfield Inn
Property entrance

The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (51 reviews)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
United States
Kavina
The price is Rp4.172.182
Rp4.589.552 total
includes taxes & fees
3 Apr - 4 Apr
The Woodstocker B&B
Apartment (3 Bedrooms) | Interior

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
4.0 star property
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"We travelled to Vermont to experience the total eclipse of the sun with my so, daughter and her partner. It was an incredible experience, made all that more comfortable by being able to stay in this beautiful apartment. Next time we ate in that area we will not hesitate to book again. Thanks"
United States
alistair
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
Apartment (2 Bedrooms) | Interior

Updated Vintage Apartment < 1/2 Mi to Main St

Updated Vintage Apartment < 1/2 Mi to Main St
4.0 star property
Keene
Updated Vintage Apartment < 1/2 Mi to Main St
Apartment (3 Bedrooms) | Interior

Renovated Ski-in/ski-out Peru Condo at Bromley Mtn

Renovated Ski-in/ski-out Peru Condo at Bromley Mtn
4.0 star property
Bromley Mountain
6.0 out of 10, (2 reviews)
"Location right next to Bromley Ski Area- easy access to the mountain and short drive to Manchester. Comfortable for our family of 6. Communication with the owner was very easy. "
United States
Jaclyn
Renovated Ski-in/ski-out Peru Condo at Bromley Mtn
Apartment (2 Bedrooms) | Interior

Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!

Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
4.0 star property
West Dover
Dover Condo w/ Grill & Balcony: 3 Mi to Mt Snow!
Apartment (2 Bedrooms) | Interior

West Dover Townhome: Hot Tub, 2 Mi to Mount Snow!

West Dover Townhome: Hot Tub, 2 Mi to Mount Snow!
4.0 star property
West Dover
West Dover Townhome: Hot Tub, 2 Mi to Mount Snow!
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chester.
The Weston

The Weston

630 Main St Weston VT
The price is Rp7.607.250 per night from 18 Mar to 19 Mar
Rp7.607.250
Rp8.291.902 total
18 Mar - 19 Mar
includes taxes & fees
10/10 Exceptional! (9 reviews)
Still don't see what you're looking for?
See all properties in Chester.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

See all hotels in Chester
aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Top Chester Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"The breakfast and staff were AMAZING! Freshly made scrambled eggs, bacon, sausage patties, french toast, waffles, Cabot yogurt with all the fixings, dry cereal, hot oatmeal, breads, muffins, danish, etc. Everything was delicious and well presented as well! Forgot to mention freshly gound coffee! YUM! KUDOS!"
Elizabeth 2-night trip
Posted 2 days ago
On The River Inn
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Hotel was lovely. Beautifully appointed. Staff was excellent and very helpful. "
Kenneth 4-night trip
Posted 8 days ago
Kimpton Taconic Hotel by IHG

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chester?
With Expedia's sort and search filters, scoring a terrific deal on a 4-star hotel in Chester just got simpler. Start by keying in your chosen arrival date and length of your holiday. Then list the results by price and choose a property that best fits your style and budget.

  • Search for the lowest price from Rp8.291.902

What's the difference between 5-star and 4-star hotels in Chester?
Offering an inviting traveller experience and upscale décor, 4-star hotels are an excellent option for your Chester break. These kinds of accommodation generally come with loads of handy amenities that make it a breeze to unpack and unwind — think complimentary bathrobes, gyms and pools. Or live the high life at a 5-star hotel designed to indulge you in luxury perks and amenities. On-site health clubs, oversized bathrooms and gourmet dining are typically featured at these deluxe retreats.
Does Chester have any 4-star all-inclusive resorts?
Finding holiday bliss in Chester is as easy as entering in your dates and selecting our "All inclusive" filter. Stay and play where almost everything is already taken care of like your meals, accommodation, entertainment and activities, or opt for a standard 4-star resort in or around this top destination.